Cyrus E. Cheslak

        Associate
        Contact Info
        Cyrus E. Cheslak Cyrus E. Cheslak

        Cyrus is a dedicated, hands-on problem-solver who meets his client’s needs and guides them to successful outcomes in a wide range of civil litigation and professional liability matters.

        As a member of Verrill’s litigation group, Cyrus uses his research and writing skills and his background in politics to provide thoughtful, methodical, and pragmatic representation to a variety of clients, from large corporations to individuals, tailoring his approach to meet the case and client’s needs. Cyrus advocates for clients in state and federal court, from pre-trial through appellate stages, as well as before state commissions, boards, and panels.

        During law school, Cyrus was a student attorney for the Cumberland County District Attorney’s Office and Cumberland Legal Aid Clinic, and a judicial expert to the Honorable Kermit V. Lipez of the United States Court of Appeals for the First Circuit. He also served as a teaching assistant for the Legal Research & Writing Program and tutored first-year law students. Cyrus was also the Head Case Note & Comment Editor of the Maine Law Review and competed on Maine Law’s Trial Competition and Moot Court Teams. After graduating magna cum laude from the University of Maine School of Law, Cyrus clerked for the Honorable Thomas E. Humphrey of the Maine Supreme Judicial Court, where he continued to hone his research and writing skills in an appellate setting.

        Prior to law school, Cyrus was an aide to United States Senator Susan M. Collins in Washington D.C., where he worked on a variety of legislative matters including health care, agriculture, and nutrition policy, and managed the office’s administrative operations. Cyrus maintains a strong interest in the legislative and regulatory fields.

        Cyrus now lives in Portland with his family and two dogs, where he enjoys hosting backyard barbeques, visiting Maine’s famed breweries, and hiking and exploring Maine’s natural beauty with his kids.

        Services/Industries

        Education

        • University of Maine School of Law (J.D., magna cum laude)
          • Head Case Note & Comment Editor – Maine Law Review
        • Franklin & Marshall College (B.A.)

        Public Service

        • Maine State Bar Association Leadership Academy

        Bar Admissions

        • Maine
        • Massachusetts

        Court and Other Admissions

        • U.S. District Court for the District of Maine

        Memberships

        • Maine State Bar Association
        • Tri-State Defense Lawyers Association
        • Cumberland Bar Association

        Honors

        • Best Brief, Craven Moot Court Competition
        • Faculty Significant Achievement Award
        • Named to New England Super Lawyers Rising Stars list under Civil Litigation: Defense

        Learn more about the third-party ratings, rankings, and selection processes used for inclusion.

        Clerkships

        • Maine Supreme Judicial Court, Justice Humphrey
        Events
        When: June 24, 2026 at 11:00am - 12:00pm Next Week
        Location: Webinar

        Firm Highlights

        Press Releases

        34 Verrill Attorneys, Across Four Offices, Recognized in the 2026 Chambers USA Guide

        BOSTON, Massachusetts, PORTLAND, Maine, WESTPORT, Connecticut, and WASHINGTON, D.C. – Verrill has been recognized as a Leading Firm in 14...
        Blog

        Will the Knicks Beat the Spurs? (Are Prediction Market Event Contracts Gambling?)

        For those of you who like to keep score, currently 18 states are engaged in litigation over prediction markets, such as Kalshi and Polymarket,...
        Alerts and Newsletters

        DOJ Announces Faster Review and Enhanced Enforcement for Benefits-Fraud FCA Matters

        On May 27, 2026, the U.S. Department of Justice (DOJ) Civil Division issued a new memorandum, “Accelerating Review and Enhancing Enforcement in...
        Alerts and Newsletters

        DOJ Announces Minnesota Health Care Fraud Takedown; Signals Intensified Medicaid Enforcement Nationwide

        On May 21, the Department of Justice (“DOJ”) announced a first-of-its kind Minnesota Health Care Fraud Takedown charging 15 defendants, including...
        Media Mentions

        Lauren Galvin Quoted in Massachusetts Lawyers Weekly on Arbitration and Anti-SLAPP Protections

        Verrill Partner Lauren Galvin was recently featured in a Massachusetts Lawyers Weekly article highlighting a notable Superior Court decision...
        Blog

        Section 530A Accounts: What Employers Should Consider Before Offering Contributions to “Trump” Accounts

        Section 530A accounts, commonly referred to as Trump accounts, have attracted attention since the enactment of the One Big Beautiful Bill Act in...
        Blog

        Navigating PBM Reform: Regulatory Changes, Market Shifts, and Practical Guidance for ERISA Fiduciaries

        Pharmacy Benefit Manager (“PBM”) arrangements have long relied on rebates with limited transparency into true drug costs. Recent regulatory and...
        Blog

        DOL’s Proposed Regulation on Selecting Alternative Investments: Broad Implications for 401(k) and 403(b) Plan Fiduciaries

        On March 30, 2026, the Department of Labor issued a proposed regulation purporting to implement an executive order to expand access to “alternative...
        Press Releases

        Verrill Welcomes Private Clients & Fiduciary Services Attorney Gracie Castle

        BOSTON, Massachusetts – Verrill is pleased to welcome Gracie Castle to the firm’s Private Clients & Fiduciary Services Group as an Associate,...
        Published Works

        Francesco De Vito Authors Article in the Journal of the American College of Mortgage Attorneys

        Verrill Partner Frank De Vito authored an article featured in the Spring 2026 issue of The Abstract, the journal of the American College of Mortgage...
        Alerts and Newsletters

        Recent FinCEN Advisory Highlights Rising Health Care Fraud Risk for Financial Institutions

        As the federal government intensifies its “whole of government” approach to combat fraud, waste, and abuse, particularly in Federal Health Care...
        Press Releases

        Two Verrill Attorneys Featured in the 2026 Lawdragon 500 Leading Global Bankruptcy & Restructuring Lawyers List

        PORTLAND, Maine – Verrill attorneys Roger A. Clement, Jr. and Robert J. Keach have been featured in the 2026 Lawdragon 500 Leading Global...